diff --git a/cmd/workon.go b/cmd/workon.go
index ef07346..639aec2 100644
--- a/cmd/workon.go
+++ b/cmd/workon.go
@@ -92,6 +92,8 @@ func runWorkOn(cmd *cobra.Command, target string, step string, execCmd []string)
 
 	credEnvVars := creds.EnvVars()
 
+	ptdRoot := helpers.GetTargetsConfigPath()
+
 	// Start proxy if needed (non-fatal)
 	proxyFile := path.Join(internal.DataDir(), "proxy.json")
 	stopProxy, err := kube.StartProxy(cmd.Context(), t, proxyFile)
@@ -173,6 +175,7 @@ func runWorkOn(cmd *cobra.Command, target string, step string, execCmd []string)
 		for k, v := range credEnvVars {
 			shellCommand.Env = append(shellCommand.Env, k+"="+v)
 		}
+		shellCommand.Env = append(shellCommand.Env, "PTD_ROOT="+ptdRoot)
 		if kubeconfigPath != "" {
 			shellCommand.Env = append(shellCommand.Env, "KUBECONFIG="+kubeconfigPath)
 		}
@@ -210,6 +213,7 @@ func runWorkOn(cmd *cobra.Command, target string, step string, execCmd []string)
 	for k, v := range credEnvVars {
 		shellCommand.Env = append(shellCommand.Env, k+"="+v)
 	}
+	shellCommand.Env = append(shellCommand.Env, "PTD_ROOT="+ptdRoot)
 	if kubeconfigPath != "" {
 		shellCommand.Env = append(shellCommand.Env, "KUBECONFIG="+kubeconfigPath)
 	}
diff --git a/lib/azure/proxy.go b/lib/azure/proxy.go
index a39ba22..09bc01e 100644
--- a/lib/azure/proxy.go
+++ b/lib/azure/proxy.go
@@ -7,7 +7,6 @@ import (
 	"os"
 	"os/exec"
 	"os/signal"
-	"regexp"
 	"time"
 
 	"github.com/posit-dev/ptd/lib/helpers"
@@ -22,6 +21,7 @@ type ProxySession struct {
 	tunnelCommand *exec.Cmd
 	socksCommand  *exec.Cmd
 	localPort     string
+	sshKeyPath    string // temp file for bastion SSH key, cleaned up on Stop
 
 	runningProxy *proxy.RunningProxy
 	isReused     bool // indicates if the session is reused from an existing running proxy
@@ -88,16 +88,10 @@ func (p *ProxySession) Start(ctx context.Context) error {
 		return err
 	}
 
-	bastionName, err := p.target.BastionName(ctx)
-
-	if err != nil {
-		slog.Error("Error getting bastion name", "error", err)
-	}
-
-	jumpBoxId, err := p.target.JumpBoxId(ctx)
-
+	bastionInfo, err := p.target.BastionInfo(ctx)
 	if err != nil {
-		slog.Error("Error getting jump box ID", "error", err)
+		slog.Error("Error getting bastion info", "error", err)
+		return fmt.Errorf("failed to get bastion info: %w", err)
 	}
 
 	// Determine which resource group to use for the bastion tunnel
@@ -114,25 +108,32 @@ func (p *ProxySession) Start(ctx context.Context) error {
 		return fmt.Errorf("Resource Group name is empty, cannot continue.")
 	}
 
-	// HACK: at the moment, the ssh key is written to a path and named based on the bastion name.
-	// This is a temporary workaround to remove the "-host" suffix from the bastion name, since that isn't in the key name
-	r := regexp.MustCompile(`-host.*`)
-	bastionSshKeyName := r.ReplaceAllString(bastionName, "")
+	// Write the SSH private key from Pulumi state to a temp file (cleaned up in Stop)
+	sshKeyFile, err := os.CreateTemp("", "ptd-bastion-ssh-*")
+	if err != nil {
+		return fmt.Errorf("failed to create temp file for SSH key: %w", err)
+	}
+	if _, err := sshKeyFile.WriteString(bastionInfo.SSHPrivateKey); err != nil {
+		sshKeyFile.Close()
+		os.Remove(sshKeyFile.Name())
+		return fmt.Errorf("failed to write SSH key: %w", err)
+	}
+	sshKeyFile.Close()
+	p.sshKeyPath = sshKeyFile.Name()
 
 	// build the command to start the bastion tunnel, this will connect jumpbox:22 to localhost:22001 (enabling SSH connection via separate command)
 	p.tunnelCommand = exec.CommandContext(
 		ctx,
 		p.azCliPath,
 		"network", "bastion", "tunnel",
-		"--name", bastionName,
+		"--name", bastionInfo.Name,
 		"--resource-group", resourceGroupName,
-		"--target-resource-id", jumpBoxId,
+		"--target-resource-id", bastionInfo.JumpBoxID,
 		"--resource-port", "22",
 		"--port", "22001",
 	)
 
 	// build the command to start the SOCKS proxy via SSH, using the jumpbox tunnel from above
-	// ssh -ND 1080 ptd-admin@localhost -p 22001 -i ~/.ssh/bas-ptd-madrigal01-production-bastion
 	p.socksCommand = exec.CommandContext(
 		ctx,
 		"ssh",
@@ -141,7 +142,7 @@ func (p *ProxySession) Start(ctx context.Context) error {
 		"-p", "22001",
 		"-o", "StrictHostKeyChecking=no",
 		"-o", "UserKnownHostsFile=/dev/null",
-		"-i", fmt.Sprintf("%s/.ssh/%s", os.Getenv("HOME"), bastionSshKeyName))
+		"-i", p.sshKeyPath)
 
 	// set the environment variables for the command
 	// add each az env var to command
@@ -150,7 +151,7 @@ func (p *ProxySession) Start(ctx context.Context) error {
 		p.socksCommand.Env = append(p.socksCommand.Env, fmt.Sprintf("%s=%s", k, v))
 	}
 
-	slog.Debug("Starting Azure bastion tunnel", "bastion_name", bastionName, "resource_group", resourceGroupName, "tunnel_port", "22001", "target_port", "22")
+	slog.Debug("Starting Azure bastion tunnel", "bastion_name", bastionInfo.Name, "resource_group", resourceGroupName, "tunnel_port", "22001", "target_port", "22")
 	if ctx.Value("verbose") != nil && ctx.Value("verbose").(bool) {
 		slog.Debug("Verbose turned on, attaching command output to stdout and stderr")
 		p.tunnelCommand.Stdout = os.Stdout
@@ -201,6 +202,10 @@ func (p *ProxySession) Start(ctx context.Context) error {
 }
 
 func (p *ProxySession) Stop() error {
+	if p.sshKeyPath != "" {
+		os.Remove(p.sshKeyPath)
+	}
+
 	if p.isReused {
 		slog.Debug("Proxy session was reused, not stopping", "target", p.target.Name(), "local_port", p.localPort)
 		return nil
diff --git a/lib/azure/target.go b/lib/azure/target.go
index 9be7159..a89c72e 100644
--- a/lib/azure/target.go
+++ b/lib/azure/target.go
@@ -166,10 +166,18 @@ func (t Target) fullPulumiEnvVars(ctx context.Context) (map[string]string, error
 	return creds.EnvVars(), nil
 }
 
-func (t Target) BastionName(ctx context.Context) (string, error) {
+// BastionInfo holds the bastion connection details from the persistent stack.
+type BastionInfo struct {
+	Name          string
+	JumpBoxID     string
+	SSHPrivateKey string
+}
+
+// BastionInfo retrieves bastion connection details from the persistent stack outputs.
+func (t Target) BastionInfo(ctx context.Context) (*BastionInfo, error) {
 	envVars, err := t.fullPulumiEnvVars(ctx)
 	if err != nil {
-		return "", err
+		return nil, err
 	}
 
 	persistentStack, err := pulumi.NewPythonPulumiStack(
@@ -185,57 +193,35 @@ func (t Target) BastionName(ctx context.Context) (string, error) {
 		false,
 	)
 	if err != nil {
-		return "", err
+		return nil, err
 	}
 
-	persistentOutputs, err := persistentStack.Outputs(ctx)
+	outputs, err := persistentStack.Outputs(ctx)
 	if err != nil {
-		return "", err
-	}
-
-	if _, ok := persistentOutputs["bastion_name"]; !ok {
-		return "", fmt.Errorf("bastion_name output not found in persistent stack outputs")
+		return nil, err
 	}
 
-	bastionName := persistentOutputs["bastion_name"].Value.(string)
+	info := &BastionInfo{}
 
-	return bastionName, nil
-}
-
-func (t Target) JumpBoxId(ctx context.Context) (string, error) {
-	envVars, err := t.fullPulumiEnvVars(ctx)
-	if err != nil {
-		return "", err
-	}
-
-	persistentStack, err := pulumi.NewPythonPulumiStack(
-		ctx,
-		"azure",
-		"workload",
-		"persistent",
-		t.Name(),
-		t.Region(),
-		t.PulumiBackendUrl(),
-		t.PulumiSecretsProviderKey(),
-		envVars,
-		false,
-	)
-	if err != nil {
-		return "", err
+	if v, ok := outputs["bastion_name"]; ok {
+		info.Name = v.Value.(string)
+	} else {
+		return nil, fmt.Errorf("bastion_name output not found in persistent stack outputs")
 	}
 
-	persistentOutputs, err := persistentStack.Outputs(ctx)
-	if err != nil {
-		return "", err
+	if v, ok := outputs["bastion_jumpbox_id"]; ok {
+		info.JumpBoxID = v.Value.(string)
+	} else {
+		return nil, fmt.Errorf("bastion_jumpbox_id output not found in persistent stack outputs")
 	}
 
-	if _, ok := persistentOutputs["bastion_jumpbox_id"]; !ok {
-		return "", fmt.Errorf("bastion_jumpbox_id output not found in persistent stack outputs")
+	if v, ok := outputs["bastion_ssh_private_key"]; ok {
+		info.SSHPrivateKey = v.Value.(string)
+	} else {
+		return nil, fmt.Errorf("bastion_ssh_private_key output not found in persistent stack outputs")
 	}
 
-	jumpBoxId := persistentOutputs["bastion_jumpbox_id"].Value.(string)
-
-	return jumpBoxId, nil
+	return info, nil
 }
 
 // HashName returns an obfuscated name for the target that can be used as a unique identifier.
diff --git a/python-pulumi/src/ptd/pulumi_resources/azure_bastion.py b/python-pulumi/src/ptd/pulumi_resources/azure_bastion.py
index 2894ad1..e1cdc6f 100644
--- a/python-pulumi/src/ptd/pulumi_resources/azure_bastion.py
+++ b/python-pulumi/src/ptd/pulumi_resources/azure_bastion.py
@@ -1,7 +1,6 @@
 import pulumi
 import pulumi_tls as tls
 from pulumi_azure_native import compute, network
-from pulumi_command import local
 
 
 class AzureBastion(pulumi.ComponentResource):
@@ -50,19 +49,6 @@ def __init__(
             algorithm="ED25519",
         )
 
-        # write the private key to a file on the local machine
-        # this needs to be repeated by any engineer who wants to access the jumpbox
-        local.run_output(
-            command=pulumi.Output.format(
-                "FILE=~/.ssh/{1}; "
-                'if [ ! -f "$FILE" ]; then '
-                'echo \'{0}\' > "$FILE" && chmod 600 "$FILE"; '
-                'else echo "File $FILE already exists, skipping."; fi',
-                self.jumpbox_ssh_key.private_key_openssh,
-                name,
-            ),
-        )
-
         # Create a Public IP for Bastion
         self.public_ip = network.PublicIPAddress(
             f"{name}-pip",
diff --git a/python-pulumi/src/ptd/pulumi_resources/azure_workload_persistent.py b/python-pulumi/src/ptd/pulumi_resources/azure_workload_persistent.py
index da80cd8..bfa2ccb 100644
--- a/python-pulumi/src/ptd/pulumi_resources/azure_workload_persistent.py
+++ b/python-pulumi/src/ptd/pulumi_resources/azure_workload_persistent.py
@@ -96,6 +96,7 @@ def __init__(
             "app_gateway_subnet_id": self.app_gateway_subnet.id,
             "bastion_name": self.bastion.bastion_host.name,
             "bastion_jumpbox_id": self.bastion.jumpbox_host.id,
+            "bastion_ssh_private_key": self.bastion.jumpbox_ssh_key.private_key_openssh,
             "mimir_password": self.mimir_password.result,
             "private_subnet_name": self.private_subnet.name,
             "private_subnet_cidr": self.private_subnet.address_prefix,